#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/81/2238136.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2238136
loop_
_publ_author_name
'Suchetan, P. A.'
'Sreenivasa, S.'
'Palakshamurthy, B. S.'
'Madhu Chakrapani Rao, T.'
Vijithkumar
_publ_section_title
;
 N'-Hydroxypyridine-2-carboximidamide
;
_journal_coeditor_code           BT6916
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1180
_journal_paper_doi               10.1107/S1600536813017418
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H7 N3 O'
_chemical_formula_moiety         'C6 H7 N3 O'
_chemical_formula_sum            'C6 H7 N3 O'
_chemical_formula_weight         137.15
_chemical_name_systematic
;
N'-Hydroxypyridine-2-carboximidamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.468(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.367(5)
_cell_length_b                   4.6382(11)
_cell_length_c                   13.003(3)
_cell_measurement_reflns_used    1088
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     1242.0(5)
_computing_cell_refinement       'APEX2 and SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 1.03
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8242
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1086
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0379P)²+0.8786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                982
_reflns_number_total             1086
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bt6916.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2238136
_cod_database_fobs_code          2238136
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.19134(4) 0.1826(2) 0.26040(7) 0.0207(3) Uani d . 1 1
H H1N2 0.0896(7) 0.225(3) 0.1797(12) 0.027(4) Uiso d D 1 1
H H2N2 0.0456(6) 0.081(3) 0.0861(11) 0.027(4) Uiso d D 1 1
H H1 0.2316(9) 0.260(4) 0.2779(14) 0.043(5) Uiso d . 1 1
C C1 0.12315(6) -0.2716(3) 0.03188(9) 0.0154(3) Uani d . 1 1
C C2 0.17439(6) -0.4236(3) 0.01036(10) 0.0189(3) Uani d . 1 1
H H2 0.2167 -0.3964 0.0520 0.023 Uiso calc R 1 1
C C3 0.16144(6) -0.6149(3) -0.07361(10) 0.0208(3) Uani d . 1 1
H H3 0.1949 -0.7164 -0.0904 0.025 Uiso calc R 1 1
C C4 0.09770(6) -0.6536(3) -0.13259(10) 0.0211(3) Uani d . 1 1
H H4 0.0874 -0.7834 -0.1891 0.025 Uiso calc R 1 1
C C5 0.05004(6) -0.4948(3) -0.10538(10) 0.0203(3) Uani d . 1 1
H H5 0.0073 -0.5229 -0.1449 0.024 Uiso calc R 1 1
C C6 0.13390(5) -0.0595(3) 0.12070(9) 0.0147(3) Uani d . 1 1
N N1 0.06133(5) -0.3023(2) -0.02561(8) 0.0176(3) Uani d . 1 1
N N2 0.08163(5) 0.0824(2) 0.13540(9) 0.0179(3) Uani d D 1 1
N N3 0.19228(5) -0.0259(2) 0.18081(8) 0.0175(3) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 O1 H1 104.9(11)
N1 C1 C2 123.03(11)
N1 C1 C6 115.35(10)
C2 C1 C6 121.61(11)
C3 C2 C1 118.91(12)
C3 C2 H2 120.5
C1 C2 H2 120.5
C2 C3 C4 118.86(12)
C2 C3 H3 120.6
C4 C3 H3 120.6
C5 C4 C3 118.28(12)
C5 C4 H4 120.9
C3 C4 H4 120.9
N1 C5 C4 124.19(12)
N1 C5 H5 117.9
C4 C5 H5 117.9
N3 C6 N2 123.75(11)
N3 C6 C1 118.26(10)
N2 C6 C1 117.97(10)
C1 N1 C5 116.69(10)
C6 N2 H1N2 116.3(10)
C6 N2 H2N2 119.9(10)
H1N2 N2 H2N2 118.9(14)
C6 N3 O1 108.89(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.4201(13)
O1 H1 0.903(18)
C1 N1 1.3407(16)
C1 C2 1.3918(17)
C1 C6 1.4878(17)
C2 C3 1.3765(18)
C2 H2 0.9300
C3 C4 1.3849(19)
C3 H3 0.9300
C4 C5 1.3773(18)
C4 H4 0.9300
C5 N1 1.3408(16)
C5 H5 0.9300
C6 N3 1.2928(16)
C6 N2 1.3532(16)
N2 H1N2 0.862(13)
N2 H2N2 0.859(13)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N3 4 0.903(18) 1.859(19) 2.7537(14) 170.5(17)
N2 H2N2 N1 5 0.859(13) 2.438(14) 3.1753(16) 144.3(13)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C1 C2 C3 -0.07(18)
C6 C1 C2 C3 -179.35(11)
C1 C2 C3 C4 -1.19(18)
C2 C3 C4 C5 0.96(18)
C3 C4 C5 N1 0.6(2)
N1 C1 C6 N3 178.22(10)
C2 C1 C6 N3 -2.45(17)
N1 C1 C6 N2 -0.29(16)
C2 C1 C6 N2 179.05(11)
C2 C1 N1 C5 1.51(17)
C6 C1 N1 C5 -179.17(10)
C4 C5 N1 C1 -1.77(18)
N2 C6 N3 O1 -0.96(16)
C1 C6 N3 O1 -179.38(9)
